4-Azidocinnoline-Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe.
| Title: | 4-Azidocinnoline-Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe. |
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| Authors: | Danilkina NA; Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.; Andrievskaya EV; Faculty of Chemistry, Belarusian State University, Leningradskaya Str. 14, 220006 Minsk, Belarus.; Vasileva AV; Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.; Lyapunova AG; Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.; Rumyantsev AM; Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.; Kuzmin AA; Institute of Cytology, Russian Academy of Sciences, St. Petersburg, Tikhoretsky Avenue 4, 194064 Saint Petersburg, Russia.; Bessonova EA; Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.; Balova IA; Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia. |
| Source: | Molecules (Basel, Switzerland) [Molecules] 2021 Dec 09; Vol. 26 (24). Date of Electronic Publication: 2021 Dec 09. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Basel, Switzerland : MDPI, c1995- |
| MeSH Terms: | Fluorescent Dyes*/chemical synthesis ; Fluorescent Dyes*/chemistry ; Fluorescent Dyes*/pharmacokinetics ; Fluorescent Dyes*/pharmacology; Hep G2 Cells ; Humans ; Microscopy, Fluorescence ; Spectrometry, Fluorescence |
| Abstract: | A new type of fluorogenic and fluorochromic probe based on the reduction of weakly fluorescent 4-azido-6-(4-cyanophenyl)cinnoline to the corresponding fluorescent cinnoline-4-amine was developed. We found that the fluorescence of 6-(4-cyanophenyl)cinnoline-4-amine is strongly affected by the nature of the solvent. The fluorogenic effect for the amine was detected in polar solvents with the strongest fluorescence increase in water. The environment-sensitive fluorogenic properties of cinnoline-4-amine in water were explained as a combination of two types of fluorescence mechanisms: aggregation-induced emission (AIE) and excited state intermolecular proton transfer (ESPT). The suitability of an azide-amine pair as a fluorogenic probe was tested using a HepG2 hepatic cancer cell line with detection by fluorescent microscopy, flow cytometry, and HPLC analysis of cells lysates. The results obtained confirm the possibility of the transformation of the azide to amine in cells and the potential applicability of the discovered fluorogenic and fluorochromic probe for different analytical and biological applications in aqueous medium. |
| References: | Chem Sci. 2017 Mar 1;8(3):2107-2114. (PMID: 28348729); Acc Chem Res. 2017 Feb 21;50(2):366-375. (PMID: 28067047); Analyst. 2015 Nov 7;140(21):7165-9. (PMID: 26401525); Molecules. 2020 Feb 24;25(4):. (PMID: 32102403); Sens Actuators B Chem. 2021 Feb 15;329:. (PMID: 35058674); Chem Rev. 2015 Nov 11;115(21):11718-940. (PMID: 26492387); Spectrochim Acta A Mol Biomol Spectrosc. 2021 May 5;252:119515. (PMID: 33578122); Molecules. 2016 Oct 24;21(10):. (PMID: 27783053); Chemistry. 2019 Nov 22;25(65):14972-14982. (PMID: 31509279); Chembiochem. 2012 May 29;13(8):1116-20. (PMID: 22514188); J Am Chem Soc. 2019 Sep 25;141(38):15111-15120. (PMID: 31436971); Chemistry. 2021 Mar 17;27(16):5057-5073. (PMID: 33017499); Org Biomol Chem. 2019 Feb 13;17(7):1813-1816. (PMID: 30534778); Org Biomol Chem. 2014 Dec 14;12(46):9307-20. (PMID: 25315039); Proc Natl Acad Sci U S A. 2014 Apr 15;111(15):5456-61. (PMID: 24706769); Bioorg Med Chem Lett. 2019 Aug 15;29(16):2354-2357. (PMID: 31196712); Chemistry. 2016 Apr 25;22(18):6382-8. (PMID: 27010966); Talanta. 2019 Apr 1;195:850-856. (PMID: 30625627); Chem Sci. 2020 Dec 15;12(4):1220-1226. (PMID: 34163883); Chem Sci. 2019 Aug 16;10(34):7835-7851. (PMID: 31762967); J Am Chem Soc. 2004 Nov 24;126(46):15046-7. (PMID: 15547999); Chem Commun (Camb). 2013 May 10;49(37):3890-2. (PMID: 23549590); Angew Chem Int Ed Engl. 2006 Nov 13;45(44):7364-7. (PMID: 17036290); ACS Cent Sci. 2017 Jan 25;3(1):20-30. (PMID: 28149949); Bioconjug Chem. 2014 Jul 16;25(7):1370-4. (PMID: 24932756); J Org Chem. 2017 Dec 1;82(23):12153-12161. (PMID: 29090913); Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2408-10. (PMID: 23339134); Org Biomol Chem. 2014 Apr 28;12(16):2514-8. (PMID: 24618745); Chemistry. 2021 May 26;27(30):8040-8047. (PMID: 33904607); Beilstein J Org Chem. 2015 Mar 20;11:373-84. (PMID: 25977711); J Phys Chem A. 2011 Dec 15;115(49):14129-36. (PMID: 22026497); Chem Rev. 2020 May 27;120(10):4301-4354. (PMID: 32356973); Angew Chem Int Ed Engl. 2009;48(8):1498-500. (PMID: 19145623); Biochemistry (Mosc). 2007 Jan;72(1):1-20. (PMID: 17309432); Bioconjug Chem. 2015 Aug 19;26(8):1519-32. (PMID: 26086070); Chem Rec. 2021 Oct;21(10):2782-2807. (PMID: 33570242); Chem Soc Rev. 2015 Jul 7;44(13):4228-38. (PMID: 25374162); Angew Chem Int Ed Engl. 2021 Jul 12;60(29):15724-15742. (PMID: 32432807); Org Lett. 2004 Nov 25;6(24):4603-6. (PMID: 15548086); Molecules. 2019 Jun 27;24(13):. (PMID: 31252657); Chemistry. 2019 Jul 2;25(37):8805-8812. (PMID: 31054168); Proc Natl Acad Sci U S A. 2019 Oct 8;116(41):20303-20308. (PMID: 31554699); Chem Commun (Camb). 2021 Mar 28;57(25):3099-3102. (PMID: 33625440); Methods Appl Fluoresc. 2015 Sep 08;3(4):042001. (PMID: 29148505) |
| Grant Information: | 21-13-00218 Russian Science Foundation; 20-03-00117 Russian Foundation for Basic Research |
| Contributed Indexing: | Keywords: AIE and ESPT fluorescence mechanisms; amines; azides; cinnolines; environment-sensitive probe; fluorescence; fluorochromic probe; fluorogenic probe; richer cyclization |
| Substance Nomenclature: | 0 (Fluorescent Dyes) |
| Entry Date(s): | Date Created: 20211224 Date Completed: 20220211 Latest Revision: 20240404 |
| Update Code: | 20260130 |
| PubMed Central ID: | PMC8704291 |
| DOI: | 10.3390/molecules26247460 |
| PMID: | 34946541 |
| Database: | MEDLINE |
Journal Article